Game, Set, Match

Chapter 1: Womanizer

Summary: A/U Tommy Pickles has always been a huge womanizer, he can get any girl he wants then he leaves them in the dust, but what happens when he meets his match and doesn't even see it coming. Rating for language and mild adult content.

(A/N: the rugrats all attend a boarding school called St. Johns Academy in Connecticut, they all know each other except for Lil, it'll be explained in the story. Dil and Wally are in the 10th grade Tommy, Phil, Lil and Kimi are in 11th grade. Angelica, Susie and Harold are in the 12th. Pretty much everything is still the same except no one really knows Lil except for Phil)

Phil and Chuckie were sitting in a train compartment on their way to New Haven Connecticut to go to school for their 11th grade year. Phil was listening to his Ipod and Chuckie was writing a letter to his girlfriend Nicole back home in Ohio.

Kimi walked in with her luggage. Both the boys got up to help her. "Thanks guys" she said gratefully. Then she sat across from them. She looked around the compartment.

"Where's Tommy" she asked. Chuckie who had gone back to his letter looked up briefly at her and said. "He's with Lisa" Phil who had shut off his Ipod since Kimi came in said.

"No it's Laura, remember he broke up with Lisa when we got on the train this morning"

"Oh right" said Chuckie. Kimi scoffed and rolled her eyes, Tommy could be such a sleaze sometimes. She honestly didn't see what these girls saw in him, well she couldn't lie she too was under his spell once. But soon after realizing just what every other girl he hooked up with would know later on is that he would never change his ways.

Sometimes she wished that someone could bring him down a peg, make him fall in love, but that would never happen, most of the female population at St. Johns worshiped the ground he walked on and it wouldn't be long before the few that didn't were under his spell as well.

"So Phil how's things with Wally" Kimi asked. Chuckie continued writing. Phil's face went pale and he looked as if he would be sick.

"We're…we broke up at the end of the summer" he managed to get out.

"Oh I'm sorry I didn't know, are you ok" she asked

"Yea I'm ok, and it's ok, I'll be fine" he said. Kimi smiled she had been harboring a crush for Phil since last year, but decided not to act on her feelings on account of he told them that he had feelings for Wally and soon afterwards he and Wally started going out. She decided that she wasn't going to wait around this time she was going to tell him it was just a matter of finding the right time to do so.

Their compartment door opened and in walked Angelica, Susie and Harold

"Hiya losers" Angelica greeted. She said as they came into the compartment

"What she means to say is, how were your summers" said Susie smiling

"Yea what she said" said Angelica before taking a seat next to Chuckie glancing at the letter he was writing over his shoulder.

"Fine" said Kimi "what did you guys do" she asked

"I hung out wit David most of the time" said Susie. David was Susie's boyfriend of two years he started college this year so the two of them hung out as much as they could before he had to leave.

They all started to exchange stories of their summer vacation.

Meanwhile

Tommy was making out with Leslie….no Laura in an empty compartment on the train. They groping and kissing each other. Man hooking up with this girl was going to be easier than he thought. He felt his phone vibrate and he tore his lips away from hers. She continued kissing the exposed skin of his neck while unbuttoning her shirt. He reached into his pocket and pulled his phone out.

He smirked it was a text message from a girl named Kelley he had been trying to hook up with her since before he dated Lisa last year. She told him to meet her near the bathrooms in the middle of the train. He texted her back and said ok then he slightly pushed Laura off of him.

"Baby, I gotta go" he said to her sweetly

"But Tommy you just got here" she pouted

"I know babe, but I have to take care of something really quickly" he answered

"You're not going to see another girl are you" she asked

"No way babe you know you're the only girl for me" he said flashing her his most charming grin. She smiled back

"Ok don't take too long, I'll wait right here"

"Good I'll be back" he said then he kissed her one more time before exiting the compartment. As he walked down the passage way different girls he saw gave him smiles of seduction and innocence. He smiled boyishly at them all.

Once he got to the bathroom the door opened and someone pulled him in and slammed the door shut. Immediately the girl named Kelley had her hands all over him pulling his shirt up over his head and unbuckling his pants.

"Happy to see me" he asked smirking

"Shut up and kiss me" replied the girl Kelley. He obliged man it was definitely good to be him

Over in the Compartment

Phil got a text from his mother. Saying that his sister was going to be there within a matter of days.

"Shit" he cursed out loud. Everyone in the compartment looked at him funny

"What is it Phil" Kimi asked concern etching her voice. Oh well he sighed he might as well get it over with they were going to find out about her sooner or later.

"You guys remember my twin Lil right" he asked. They all nodded. "Well there's something you should know about her"

"What is she sick" asked Chuckie

"Yea sick in the head" he mumbled

"What did you say Phil" asked Susie

"I said no she's not sick" he sighed "Well then what's wrong with her" asked Chuckie finally finished with his letter.

"Let's just say she's not as innocent as she used to be"

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Some Character Descriptions for you

Tommy Pickles (16): 11th grade, 6'0" tall, athletic build, gorgeous baby blue eyes and a charming smile that could make any woman weak in the knees. Loves woman but likes to have more than one at one time.

Phil Deville (16): 11th grade 5'11" shaggy brown hair light green eyes, regular build, has gotten cuter over the years, loves playing acoustic guitar and just wants to have a good time

Chuckie Finster (17) 11th grade, 6'1" powder blue eyes shaggy red hair, got his braces taken off so he gotten to be more handsome but only has eyes for Nicole.

Kimi Finster (16): 11th grade, 5'6" still wears her hair in two pony tails but her hair is now waist length so her pony tails have gotten higher, has a little bit of a shape now so she gets a lot of attention from the opposite sex, although she only wants that type of attention from a certain someone.

Angelica Pickles (18) 12th grade, 5'8" wavy blonde hair, nice shape, still kinda mean but not as much, still the popular girl but is now showing more interest in her grades than in boys which may her closer to a different type of guy.

Susie Carmichael (17) 12th grade 5'5" still looks pretty much the same except more womanly curves, is really in love with her boyfriend but wonders if a long distance relationship can work especially when she starts to have feelings for some one else.

And finally

Lil Deville (16) 11th grade 5'7" has changed a lot over a course of the last few years, attended a special school for up and coming soccer stars up until now, wanted a change of scenery. Has the most perfect fit body do to her soccer time, is very intelligent, but is not nerdy like. Has waist length brown hair with a different color streak every week. Unlike Lil from the TV show, she loves to dress up but she also loves her sports, and she especially loves a challenge. One more thing she loves boys and they love her.

(A/N: those are just the main characters, just thought I'd give you a sneak peak of what's to come R&R, and I'll up date soon)